Polymorphism and isomorphism in biodegradable polyesters

Progress in Polymer Science (Oxford)

Volumn 34, Issue 7, 2009, Pages 605-640

  Pan, Pengju ^a   Inoue, Yoshio ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Biodegradability; Biodegradable polyester; Crystal structure; Crystallization; Isomorphism; Polymorphism

Indexed keywords

ALIPHATIC POLYESTERS; BIOCOMPATIBLE POLYMERS; BIODEGRADABLE POLYESTER; CHEMICAL SYNTHESIS; COMONOMER COMPOSITIONS; CONVENTIONAL MATERIALS; CRYSTALLINE STRUCTURES; CRYSTALLIZATION CONDITIONS; EXPLOSIVE GROWTHS; ISOMORPHISM; POLY(3 HYDROXYPROPIONATE); POLY(3-HYDROXYBUTYRATE-CO-3-HYDROXYVALERATE); POLY(BUTYLENE ADIPATE); POLY-3-HYDROXYBUTYRATE; POLYLACTIDE; POLYMORPHIC CRYSTALLIZATIONS; RANDOM COPOLYESTERS; SEMI-CRYSTALLINE POLYMERS; SOLID-STATE STRUCTURES; THERMAL BEHAVIORS; THERMAL PROPERTIES;

BIODEGRADABILITY; BIODEGRADATION; BIOLOGICAL MATERIALS; BUTENES; CRYSTAL STRUCTURE; CRYSTALLIZATION; ESTERS; FUNCTIONAL POLYMERS; HYSTERESIS MOTORS; ORGANIC POLYMERS; PHASE TRANSITIONS; PHYSICAL PROPERTIES; POLYESTERS; POLYMORPHISM; POLYPROPYLENES; SET THEORY; SODIUM COMPOUNDS; SYNTHESIS (CHEMICAL); THERMODYNAMIC PROPERTIES;

BIODEGRADABLE POLYMERS;

EID: 65449160052     PISSN: 00796700     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.progpolymsci.2009.01.003     Document Type: Review

References (219)

1. Nair L.S., and Laurencin C.T. Biodegradable polymers as biomaterials. Prog Polym Sci 32 (2007) 762-798
2. In: Doi Y., and Steinbüchel A. (Eds). Polyester III. Applications and commercial products vol. 4 (2002), Wiley-VCH, Weinheim
3. Im S.S., Kim Y.H., Yoon J.S., and Chin I.J. Bio-based polymers: recent progress (2005), Wiley-VCH, Weinheim
4. Ikada Y., and Tsuji H. Biodegradable polyesters for medical and ecological applications. Macromol Rapid Commun 21 (2000) 117-132
5. Misra S.K., Valappil S.P., Roy I., and Boccaccini A.R. Polyhydroxyalkanoate (PHA)/inorganic phase composites for tissue engineering applications. Biomacromolecules 7 (2006) 2249-2258
6. Iwata T., and Doi Y. Crystal structure and biodegradation of aliphatic polyester crystals. Macromol Chem Phys 200 (1999) 2429-2442
7. Yu L., Dean K., and Li L. Polymer blends and composites from renewable resources. Prog Polym Sci 31 (2006) 576-602
8. Doi Y. Microbial polyesters (1990), VCH publisher, New York
9. Inoue Y., and Yoshie N. Structure and physical properties of bacterially synthesized properties. Prog Polym Sci 17 (1992) 571-610
10. In: Doi Y., and Steinbüchel A. (Eds). Polyester II. Properties and chemical synthesis vol. 3b (2002), Wiley-VCH, Weinheim
11. Lenz R.W., and Marchessault R.H. Bacterial polyesters: biosynthesis, biodegradable plastics and biotechnology. Biomacromolecules 6 (2005) 1-8
12. Drumright R.E., Gruber P.R., and Henton D.E. Polylactic acid technology. Adv Mater 12 (2000) 1841-1846
13. Södergård A., and Stolt M. Properties of lactic acid based polymers and their correlation with composition. Prog Polym Sci 27 (2002) 1123-1163
14. Gupta B., Revagade N., and Hilborn J. Poly(lactic acid) fiber: an overview. Prog Polym Sci 32 (2007) 455-482
15. Gupta A.P., and Kumar V. New emerging trends in synthetic biodegradable polymers-polylactide: a critique. Eur Polym J 43 (2007) 4053-4074
16. Lim L.T., Auras R., and Rubino M. Processing technologies for poly(lactic acid). Prog Polym Sci 33 (2008) 820-852
17. Tsuji H. Poly(lactide) stereocomplexes: formation, structure, properties, degradation, and applications. Macromol Biosci 5 (2005) 569-597
18. Varma I.K., Albertsson A.C., Rajkhowa R., and Srivastava R.K. Enzyme catalyzed synthesis of polyesters. Prog Polym Sci 30 (2005) 949-981
19. Corradini P., and Guerra G. Polymorphism in polymers. Adv Polym Sci 100 (1992) 183-217
20. De Rosa C., and Auriemma F. Structure and physical properties of syndiotactic polypropylene: a highly crystalline thermoplastic elastomer. Prog Polym Sci 31 (2006) 145-237
21. Brückner S., Meille S.V., Petraccone V., and Pirozzi B. Polymorphism in isotactic polypropylene. Prog Polym Sci 16 (1991) 361-404
22. Lotz B., Wittmann J.C., and Lovinger A.J. Structure and morphology of poly(propylenes): a molecular analysis. Polymer 37 (1996) 4979-4992
23. Woo E.M., Sun Y.S., and Yang C.P. Polymorphism, thermal behavior, and crystal stability in syndiotactic polystyrene vs. its miscible blends. Prog Polym Sci 26 (2001) 945-983
24. Auriemma F., De Rosa C., and Corradini P. Solid mesophases in semicrystalline polymers: structural analysis by diffraction techniques. Adv Polym Sci 181 (2005) 1-74
25. Keller A., and Cheng S.Z.D. The role of metastability in polymer phase transitions. Polymer 39 (1998) 4461-4487
26. Cheng S.Z.D., Zhu L., Li C.Y., Honigfort P.S., and Keller A. Size effect of metastable states on semicrystalline polymer structures and morphologies. Thermochim Acta 332 (1999) 105-113
27. Gan Z., Kuwabara K., Abe H., Iwata T., and Doi Y. Metastability and transformation of polymorphic crystals in biodegradable poly(butylene adipate). Biomacromolecules 5 (2004) 371-378
28. Medellín-Rodríguez F.J., Larios-López L., Zapata-Espinoza A., Dávalos-Montoya O., Phillips P.J., and Lin J.S. Melting behavior of polymorphics: molecular weight dependence and steplike mechanisms in nylon-6. Macromolecules 37 (2004) 1799-1809
29. Zhu B., He Y., Asakawa N., Yoshie N., Nishida H., and Inoue Y. A new crystal form, polymorphism, and multi-morphology in biodegradable poly(3-hydroxypropionate). Macromol Rapid Commun 26 (2005) 581-585
30. Guerra G., Di Dino G., Centore R., Petraccone V., Obrzut J., Karasz F.E., et al. Structural characterization of vinylidene fluoride/vinyl fluoride copolymers. Makromol Chem 190 (1989) 2203-2210
31. Lovinger A.J. Ferroelectric transition in a copolymer of vinylidene fluoride and tetrafluoroethylene. Macromolecules 16 (1983) 1529-1534
32. Zhao L., and Gan Z. Effect of copolymerized butylene terephthalate chains on polymorphism and enzymatic degradation of poly(butylene adipate). Polym Degrad Stab 91 (2006) 2429-2436
33. Wittmann J.C., and Lotz B. Epitaxial crystallization of polymers on organic and polymeric substrates. Prog Polym Sci 15 (1990) 909-948
34. Cartier L., Okihara T., Ikada Y., Tsuji H., Puiggalí J., and Lotz B. Epitaxial crystallization and crystalline polymorphism of polylactides. Polymer 41 (2000) 8909-8919
35. Sun Y., Li H., Huang Y., Chen E., Zhao L., Gan Z., et al. Epitaxial crystallization of poly(butylene adipate) on highly oriented polyethylene thin film. Macromolecules 38 (2005) 2739-2743
36. Sun Y., Li H., Huang Y., Chen E., Gan Z., and Yan S. Epitaxial crystallization of poly(butylene adipate) on highly oriented isotactic polypropylene thin film. Polymer 47 (2006) 2455-2459
37. Libster D., Aserin A., and Garti N. Advanced nucleating agents for polypropylene. Polym Adv Technol 18 (2007) 685-695
38. Miyazaki T., Takeda Y., Akasaka M., Sakai M., and Hoshiko A. Preparation of isothermally crystallized γ-form poly(vinylidene fluoride) films by adding a KBr powder as a nucleating agent. Macromolecules 41 (2008) 2749-2753
39. Lotz B. Structural polymorphism of crystalline polymers: electron and atomic force microscopy contributions. Macromol Symp 94 (1995) 97-104
40. Miyata T., and Masuko T. Crystallization behavior of poly(tetramethylene succinate). Polymer 39 (1998) 1399-1404
41. Woo E.M., Wu P.L., Wu M.C., and Yan K.C. Thermal behavior of ring-band versus Maltese-Cross spherulites: case of monomorphic poly(ethylene adipate). Macromol Chem Phys 207 (2006) 2232-2243
42. Grein C., Plummer C.J.G., Kausch H.H., Germain Y., and Béguelin Ph. Influence of β nucleation on the mechanical properties of isotactic polypropylene and rubber modified isotactic polypropylene. Polymer 43 (2002) 3279-3293
43. Lovinger A.J. Ferroelectric polymers. Science 220 (1983) 1115-1121
44. Natta G., Corradini P., Sianesi D., and Morero D. Isomorphism phenomena in macromolecules. J Polym Sci 51 (1961) 527-539
45. Bluhm T.L., Hamer G.K., Marchessault R.H., Fyfe C.A., and Veregin R.P. Isodimorphism in bacterial poly(β-hydroxybutyrate-co-β-hydroxyvalerate). Macromolecules 19 (1986) 2871-2876
46. Lu X., and Windle A.H. Crystallization of random copolymers of poly(ethylene terephthalate) and poly(ethylene naphthalene-2,6-dicarboxylate). Polymer 36 (1995) 451-459
47. Lee J.H., Jeong Y.G., Lee S.C., Min B.G., and Jo W.H. Cocrystallization behavior of poly(hexamethylene terephthalate-co-hexamethylene 2,6-naphthalate) random copolymers. Polymer 43 (2002) 5263-5270
48. Yoshie N., and Inoue Y. Cocrystallization and phase segregation in blends of two bacterial polyesters. Macromol Symp 224 (2005) 59-70
49. Xu J., Xu X., Chen L., Feng L., and Chen W. Effect of composition distribution on miscibility and co-crystallization phenomena in the blends of low density polyethylene with conventional and metallocene-based ethylene-butene copolymers. Polymer 42 (2001) 3867-3874
50. Utracki L.A. Polymer alloys and blends thermodynamics and rheology (1989), Hanser Publishers, New York p. 57-65
51. Natta G., Allegra G., Bassi I.W., Carlini C., Chiellini E., and Montagnoli G. Isomorphism phenomena in isotactic poly(4-methyl-substituted α-olefins) and in isotactic poly(alkyl vinyl ethers). Macromolecules 2 (1969) 311-315
52. Patcheak T.D., and Jabarin S.A. Structure and morphology of PET/PEN blends. Polymer 42 (2001) 8975-8985
53. Nandan B., Lal B., Pandey K.N., Alam S., Kandpal L.D., and Mathur G.N. Miscibility behaviour of poly(ether ether ketone)/poly(ether ketone) blends-thermal and morphological studies. Eur Polym J 37 (2001) 2147-2151
54. Allegra G., and Bassi I.W. Isomorphism in synthetic macromolecular systems. Adv Polym Sci 6 (1969) 549-574
55. Inoue Y. Solid-state structure and properties of bacterial copolymers. J Mol Struct 441 (1998) 119-127
56. Inoue Y. Biodegradable polymers. In: Ando I., and Asakura T. (Eds). Solid state NMR of polymers (1998), Elsevier, Amsterdam 771-817
57. Okamura K., and Marchessault R.H. X-ray structure of poly(β-hydroxybutyrate). In: Romachandran G.N. (Ed). Conformation of biopolymers vol. 2 (1967), Academic Press, New York 709-720
58. Cornibert J., and Marchessault R.H. Physical properties of poly-β-hydroxybutyrate. IV. Conformational analysis and crystalline structure. J Mol Biol 71 (1972) 735-756
59. Yokouchi M., Chatani Y., Tadokoro H., Teranishi K., and Tani H. Structural studies of polyesters. 5. Molecular and crystal structures of optically active racemic poly(β-hydroxybutyrate). Polymer 14 (1973) 267-272
60. Brückner S., Meille S.V., Malpezzi L., Cesàro A., Navarini L., and Tombolini R. The structure of poly(d-(-)-β-hydroxybutyrate). A refinement based on the Rietveld method. Macromolecules 21 (1988) 967-972
61. Pazur R.J., Hocking P.J., Raymond S., and Marchessault R.H. Crystal structure of syndiotactic poly(β-hydroxybutyrate) from X-ray fiber and powder diffraction analyses and molecular modeling. Macromolecules 31 (1998) 6585-6592
62. Orts W.J., Marchessault R.H., Bluhm T.L., and Hamer G.K. Observation of strain-induced β form in poly(β-hydroxyalkanoates). Macromolecules 23 (1990) 5368-5370
63. Nishiyama Y., Tanaka T., Yamazaki T., and Iwata T. 2D NMR observation of strain-induced β-form in poly[(R)-3-hydroxybutyrate]. Macromolecules 39 (2006) 4086-4092
64. Murakami R., Sato H., Dybal J., Iwata T., and Ozaki Y. Formation and stability of β-structure in biodegradable ultra-high-molecular-weight poly(3-hydroxybutyrate) by infrared, Raman, and quantum chemical calculation studies. Polymer 48 (2007) 2672-2680
65. Yamane H., Terao K., Hiki S., and Kimura Y. Mechanical properties and higher order structure of bacterial homo poly(3-hydroxybutyrate) melt spun fibers. Polymer 42 (2001) 3241-3248
66. Aoyagi Y., Doi Y., and Iwata T. Mechanical properties and highly ordered structure of ultra-high-molecular-weight poly[(R)-3-hydroxybutyrate] films: effects of annealing and two-step drawing. Polym Degrad Stab 79 (2003) 209-216
67. Iwata T., Tsunoda T., Aoyagi Y., Kusaka S., Yonezawa N., and Doi Y. Mechanical properties of uniaxially cold-drawn films of poly([R]-3-hydroxybutyrate). Polym Degrad Stab 79 (2003) 217-224
68. Furuhashi Y., Imamura Y., Jikihara Y., and Yamane Y. Higher order structures and mechanical properties of bacterial homo poly(3-hydroxybutyrate) fibers prepared by cold-drawing and annealing processes. Polymer 45 (2004) 5703-5712
69. Iwata T., Fujita M., Aoyagi Y., Doi Y., and Fujisawa T. Time-resolved X-ray diffraction study on poly[(R)-3-hydroxybutyrate] films during two-step-drawing: generation mechanism of planar zigzag structure. Biomacromolecules 6 (2005) 1803-1809
70. Tanaka T., Fujita M., Takeuchi A., Suzuki Y., Uesugi K., Ito K., et al. Formation of highly ordered structure in poly[(R)-3-hydroxybutyrate-co-(R)-3-hydroxyvalerate] high-strength fibers. Macromolecules 39 (2006) 2940-2946
71. De Santis P., and Kovacs A.J. Molecular conformation of poly(S-lactic acid). Biopolymers 6 (1968) 299-306
72. Kalb B., and Pennings A.J. General crystallization behavior of poly(l-lactic acid). Polymer 21 (1980) 607-612
73. Hoogsteen W., Postema A.R., Pennings A.J., and ten Brinke G. Crystal structure, conformation, and morphology of solution-spun poly(l-lactide) fibers. Macromolecules 23 (1990) 634-642
74. Marega C., Marigo A., Di Noto V., Zannetti R., Martorana A., and Paganetto G. Structure and crystallization kinetics of poly(l-lactic acid). Makromol Chem 193 (1992) 1599-1606
75. Kobayashi J., Asahi T., Ichiki M., Oikawa A., Suzuki H., Watanabe T., et al. Structural and optical properties of poly-lactic acids. J Appl Phys 77 (1995) 2957-2973
76. Brizzolara D., Cantow H.J., Diederichs K., Keller E., and Domb A.J. Mechanism of the stereocomplex formation between enantiomeric poly(lactide)s. Macromolecules 29 (1996) 191-197
77. Miyata T., and Masuko T. Morphology of poly(l-lactide) solution-grown crystals. Polymer 38 (1997) 4003-4009
78. Iwata T., and Doi Y. Morphology and enzymatic degradation of poly(l-lactic acid) single crystals. Macromolecules 31 (1998) 2461-2467
79. Alemán C., Lotz B., and Puiggalí J. Crystal structure of the α-form of poly(l-lactide). Macromolecules 34 (2001) 4795-4801
80. Sasaki S., and Asakura T. Helix distortion and crystal structure of the α-form of poly(l-lactide). Macromolecules 36 (2003) 8385-8390
81. Eling B., Gogolewski S., and Pennings A.J. Biodegradable materials of poly(l-lactic acid). 1. Melt-spun and solution-spun fibres. Polymer 23 (1982) 1587-1593
82. Sawai D., Takahashi K., Imamura T., Nakamura K., Kanamoto T., and Hyon S.H. Preparation of oriented β-form poly(l-lactic acid) by solid-state extrusion. J Polym Sci Part B: Polym Phys 40 (2002) 95-104
83. Puiggalí J., Ikada Y., Tsuji H., Cartier L., Okihara T., and Lotz B. The frustrated structure of poly(l-lactide). Polymer 41 (2000) 8921-8930
84. Brant D.A., Tonelli A.E., and Flory P.J. The configurational statistics of random poly(lactic acid) chains. II. Theory. Macromolecules 2 (1969) 228-235
85. Chatani Y., Okita Y., Tadokoro H., and Yamashita Y. Structural studies of polyesters. III. Crystal structure of poly-ε-caprolactone. Polym J 1 (1970) 555-562
86. Leenslag J.W., and Pennings A.J. High-strength poly(l-lactide) fibres by a dry-spinning/hot-drawing process. Polymer 28 (1987) 1695-1702
87. Sawai D., Takahashi K., Sasashige A., Kanamoto T., and Hyon S.H. Preparation of oriented β-form poly(l-lactic acid) by solid-state coextrusion: effect of extrusion variables. Macromolecules 36 (2003) 3601-3605
88. Takahashi K., Sawai D., Yokoyama T., Kanamoto T., and Hyon S.H. Crystal transformation from the α- to the β-form upon tensile drawing of poly(l-lactic acid). Polymer 45 (2004) 4969-4976
89. Sawai D., Yokoyama T., Kanamoto T., Sungil M., Hyon S.H., and Myasnikova L.P. Crystal transformation and development of tensile properties upon drawing of poly(l-lactic acid) by solid-state coextrusion: effects of molecular weight. Macromol Symp 242 (2006) 93-103
90. Abe H., Kikkawa Y., Inoue Y., and Doi Y. Morphological and kinetic analyses of regime transition for poly[(S)-lactide] crystal growth. Biomacromolecules 2 (2001) 1007-1014
91. Tsuji H., Miyase T., Tezuka Y., and Saha S.K. Physical properties, crystallization, and spherulite growth of linear and 3-arm poly(l-lactide)s. Biomacromolecules 6 (2005) 244-254
92. Tsuji H., Tezuka Y., Saha S.K., Suzuki M., and Itsuno S. Spherulite growth of l-lactide copolymers: effects of tacticity and comonomers. Polymer 46 (2005) 4917-4927
93. Yuryev Y., Wood-Adams P., Heuzey M.C., Dubois C., and Brisson J. Crystallization of polylactide films: an atomic force microscopy study of the effects of temperature and blending. Polymer 49 (2008) 2306-2320
94. Di Lorenzo M.L. Crystallization behavior of poly(l-lactic acid). Eur Polym J 41 (2005) 569-575
95. Di Lorenzo M.L. The crystallization and melting processes of poly(l-lactic acid). Macromol Symp 234 (2006) 176-183
96. Yasuniwa M., Tsubakihara S., Iura K., Ono Y., Dan Y., and Takahashi K. Crystallization behavior of poly(l-lactic acid). Polymer 47 (2006) 7554-7563
97. Pan P., Zhu B., Kai W., Dong T., and Inoue Y. Effect of crystallization temperature on crystal modifications and crystallization kinetics of poly(l-lactide). J Appl Polym Sci 107 (2008) 54-62
98. Pan P., Kai W., Zhu B., Dong T., and Inoue Y. Polymorphous crystallization and multiple melting behavior of poly(l-lactide): molecular weight dependence. Macromolecules 40 (2007) 6898-6905
99. Ohtani Y., Okumura K., and Kawaguchi A. Crystallization behavior of amorphous poly(l-lactide). J Macromol Sci Part B: Phys B42 (2003) 875-888
100. Zhang J., Duan Y., Sato H., Tsuji H., Noda I., Yan S., et al. Crystal modifications and thermal behavior of poly(l-lactic acid) revealed by infrared spectroscopy. Macromolecules 38 (2005) 8012-8021
101. Cho T.Y., and Strobl G. Temperature dependent variations in the lamellar structure of poly(l-lactide). Polymer 47 (2006) 1036-1043
102. Kawai T., Rahman N., Matsuba G., Nishida K., Kanaya T., Nakano M., et al. Crystallization and melting behavior of poly(l-lactic acid). Macromolecules 40 (2007) 9463-9469
103. Zhang J., Tashiro K., Tsuji H., and Domb A.J. Disorder-to-order phase transition and multiple melting behavior of poly(l-lactide) investigated by simultaneous measurements of WAXD and DSC. Macromolecules 41 (2008) 1352-1357
104. Aou K., and Hsu S.L. Trichroic vibrational analysis on the α-form of poly(lactic acid) crystals using highly oriented fibers and spherulites. Macromolecules 39 (2006) 3337-3344
105. Kister G., Cassanas G., and Vert M. Effects of morphology, conformation and configuration on the IR and Raman spectra of various poly(lactic acid)s. Polymer 39 (1998) 267-273
106. Pan P., Zhu B., Kai W., Dong T., and Inoue Y. Polymorphic transition in disordered poly(l-lactide) crystals induced by annealing at elevated temperatures. Macromolecules 41 (2008) 4296-4304
107. Meaurio E., Zuza E., López-Rodríguez N., and Sarasua J.R. Conformational behavior of poly(l-lactide) studied by infrared spectroscopy. J Phys Chem B 110 (2006) 5790-5800
108. Zhang J., Tashiro K., Domb A.J., and Tsuji H. Confirmation of disorder α form of poly(l-lactic acid) by the X-ray fiber pattern and polarized IR/Raman spectra measured for uniaxially-oriented samples. Macromol Symp 242 (2006) 274-278
109. Yasuniwa M., Iura K., and Dan Y. Melting behavior of poly(l-lactic acid): effects of crystallization temperature and time. Polymer 48 (2007) 5398-5407
110. Yasuniwa M., Sakamo K., Ono Y., and Kawahara W. Melting behavior of poly(l-lactic acid): X-ray and DSC analyses of the melting process. Polymer 49 (2008) 1943-1951
111. Ikada Y., Jamshidi K., Tsuji H., and Hyon S.H. Stereocomplex formation between enantiomeric poly(lactides). Macromolecules 20 (1987) 904-906
112. Okihara T., Tsuji M., Kawaguchi A., Katayama K., Tsuji H., Hyon S.H., et al. Crystal structure of stereocomplex of poly(l-lactide) and poly(d-lactide). J Macromol Sci Phys B 30 (1991) 119-140
113. Cartier L., Okihara T., and Lotz B. Triangular polymer single crystals: stereocomplexes, twins, and frustrated structures. Macromolecules 30 (1997) 6313-6322
114. Sawai D., Tsugane Y., Tamada M., Kanamoto T., Sungil M., and Hyon S.H. Crystal density and heat of fusion for a stereo-complex of poly(l-lactic acid) and poly(d-lactic acid). J Polym Sci Part B: Polym Phys 45 (2007) 2632-2639
115. 3⋯O{double bond, long}C interaction during poly(l-lactide)/poly(d-lactide) stereocomplex formation. Macromolecules 38 (2005) 1822-1828
116. Sarasua J.R., López-Rodríguez N., Arraiza A.L., and Meaurio E. Stereoselective crystallization and specific interactions in polylactides. Macromolecules 38 (2005) 8362-8371
117. Zhang J., Tashiro K., Tsuji H., and Domb A.J. Investigation of phase transitional behavior of poly(l-lactide)/poly(d-lactide) blend used to prepare the highly-oriented stereocomplex. Macromolecules 40 (2007) 1049-1054
118. Fujita M., Sawayanagi T., Abe H., Tanaka T., Iwata T., Ito K., et al. Stereocomplex formation through reorganization of poly(l-lactic acid) and poly(d-lactic acid) crystals. Macromolecules 41 (2008) 2852-2858
119. Okamura S., Higashimura T., Tanaka A., Kato R., and Kikuchi Y. Infrared absorption spectrum of poly-β-propiolactone obtained by two kinds of ionic polymerization. Makromol Chem 54 (1962) 226-229
120. Hayashi K., Kitanishi Y., Nishii M., and Okamura S. Crystalline polymers prepared by the radiation induced solid state polymerization. Makromol Chem 47 (1961) 237-241
121. Okamura S., Hayashi K., and Kitanishi Y. Radiation-induced solid-state polymerization of ring compounds. J Polym Sci 58 (1962) 925-953
122. Wasai T., Saegusa T., and Fukukawa J. Molecular structure of poly(β-propiolactone). J Chem Soc Jpn Ind Chem Sect 67 (1964) 601-604
123. Furuhashi Y., Iwata T., Kimura Y., and Doi Y. Structural characterization and enzymatic degradation of α-, β-, and γ-crystalline forms for poly(β-propiolactone). Macromol Biosci 3 (2003) 462-470
124. Suehiro K., Chatani Y., and Tadokoro H. Structual studies of polyesters. VI. Disordered crystal structure (form II) of poly(β-propiolactone). Polym J 7 (1975) 352-358
125. Zhu B., He Y., Asakawa N., Yoshie N., Nishida H., and Inoue Y. Polymorphic crystallization and melting-recrystallization behavior of poly(3-hydroxypropionate). Macromolecules 38 (2005) 6455-6465
126. Furuhashi Y., Iwata T., Sikorski P., Atkins E., and Doi Y. Structure and morphology of the aliphatic polyester poly-β-propiolactone in solution-grown chain-folded lamellar crystals. Macromolecules 33 (2000) 9423-9431
127. Furuhashi Y., Iwata T., and Doi Y. Morphology of solution-grown poly(β-propiolactone) single crystals. J Mater Sci 36 (2001) 4307-4313
128. Zhu B., He Y., Asakawa N., Nishida H., and Inoue Y. A new crystal form favored in low molecular weight biodegradable poly(3-hydroxypropionate). Macromolecules 39 (2006) 194-203
129. Zhu B., Kai W., Pan P., Yazawa K., Nishida H., Sakurai M., et al. Polymorphic packing and dynamics of biodegradable poly(3-hydroxypropionate). J Phys Chem B 112 (2008) 9684-9692
130. Zhu B., He Y., Nishida H., Yazawa K., Ishii N., Kasuya K., et al. Crystalline-structure-dependent enzymatic degradation of polymorphic poly(3-hydroxypropionate). Biomacromolecules 9 (2008) 1221-1228
131. Asahara S., and Katayama S. Polymerization and structure of poly(β-propiolactone). J Chem Soc Jpn Ind Chem Sect 69 (1966) 2179-2188
132. Fuller C.S., and Erickson C.L. An X-ray study of some linear polyesters. J Am Chem Soc 59 (1937) 344-351
133. Fuller C.S. The investigation of synthetic linear polymers by X-rays. Chem Rev 26 (1940) 143-167
134. Minke R., and Blackwell J. Polymorphic structures of poly(tetramethylene adipate). J Macromol Sci Phys B16 (1979) 407-417
135. Minke R., and Blackwell J. Single crystals of poly(tetramethylene adipate). J Macromol Sci Phys B18 (1980) 233-255
136. Iwata T., Kobayashi S., Tabata K., Yonezawa N., and Doi Y. Crystal structure, thermal behavior and enzymatic degradation of poly(tetramethylene adipate) solution-grown chain-folded lamellar crystals. Macromol Biosci 4 (2004) 296-307
137. Noguchi K., Kondo H., Ichikawa Y., Okuyama K., and Washiyama J. Molecular and crystal structure of poly(tetramethylene adipate) α form based on synchrotron X-ray fiber diffraction. Polymer 46 (2005) 10823-10830
138. Pouget E., Almontassir A., Casas M.T., and Puiggalí J. On the crystalline structures of poly(tetramethylene adipate). Macromolecules 36 (2003) 698-705
139. Kuwabara K., Gan Z., Nakamura T., Abe H., and Doi Y. Temperature dependence of the molecular motion in the crystalline region of biodegradable poly(butylene adipate), poly(ethylene succinate), and poly(butylene succinate). Polym Degrad Stab 84 (2004) 105-114
140. Yan C., Zhang Y., Hu Y., Ozaki Y., Shen D., Gan Z., et al. Melt crystallization and crystal transition of poly(butylene adipate) revealed by infrared spectroscopy. J Phys Chem B 112 (2008) 3311-3314
141. Gan Z., Abe H., and Doi Y. Temperature-induced polymorphic crystals of poly(butylene adipate). Macromol Chem Phys 203 (2002) 2369-2374
142. Woo E.M., and Wu M.C. Thermal and X-ray analysis of polymorphic crystals, melting, and crystalline transformation in poly(butylene adipate). J Polym Sci Part B: Polym Phys 43 (2005) 1662-1672
143. Woo E.M., Yen K.C., and Wu M.C. Analysis of multiple melting behavior of spherulites comprising ring-band shell/ringless core in polymorphic poly(butylene adipate). J Polym Sci Part B: Polym Phys 46 (2008) 892-899
144. Wu M.C., and Woo E.M. Effects of α-form or β-form nuclei on polymorphic crystalline morphology of poly(butylene adipate). Polym Int 54 (2005) 1681-1688
145. Kai W., Zhu B., He Y., and Inoue Y. Crystallization of poly(butylene adipate) in the presence of nucleating agents. J Polym Sci Part B: Polym Phys 43 (2005) 2340-2351
146. Dong T., Kai W., and Inoue Y. Regulation of polymorphic behavior of poly(butylene adipate) upon complexation with α-cyclodextrin. Macromolecules 40 (2007) 8285-8290
147. Ihn K.J., Yoo E.S., and Im S.S. Structure and morphology of poly(tetramethylene succinate) crystals. Macromolecules 28 (1995) 2460-2464
148. Ichikawa Y., Kondo H., Igarashi Y., Noguchi K., Okuyama K., and Washiyama J. Crystal structures of α and β forms of poly(tetramethylene succinate). Polymer 41 (2000) 4719-4727
149. Ichikawa Y., Suzuki J., Washiyama J., Moteki Y., Noguchi K., and Okuyama K. Strain-induced crystal modification in poly(tetramethylene succinate). Polymer 35 (1994) 3338-3339
150. Ichikawa Y., Washiyama J., Moteki Y., Noguchi K., and Okuyama K. Crystal transitions mechanism in poly(tetramethylene succinate). Polym J 27 (1995) 1230-1238
151. Tashiro K., Nakai Y., Kobayashi M., and Tadokoro H. Solid-state transition of poly(butylene terephthalate) induced by mechanical deformation. Macromolecules 13 (1980) 137-145
152. 13C NMR. Polymer 43 (2002) 1447-1451
153. Ueda A.S., Chatani Y., and Tadokoro H. Structure studies of polyesters. IV. Molecular and crystal structure of poly(ethylene succinate) and poly(ethylene oxalate). Polym J 2 (1971) 387-397
154. Ichikawa Y., Washiyama J., Moteki Y., Noguchi K., and Okuyama K. Crystal modification in poly(ethylene succinate). Polym J 27 (1995) 1264-1266
155. Ichikawa Y., Noguchi K., Okuyama K., and Washiyama J. Crystal transition mechanisms in poly(ethylene succinate). Polymer 42 (2001) 3703-3708
156. Bloembergen S., Holden D.A., Hamer G.K., Bluhm T.L., and Marchessault R.H. Studies of composition and crystallinity of bacterial poly(β-hydroxybutyrate-co-β-hydroxyvalerate). Macromolecules 19 (1986) 2865-2871
157. Orts W.J., Romansky M., and Guillet J.E. Measurement of the crystallinity of poly(β-hydroxybutyrate-co-β-hydroxyvalerate) copolymers by inverse gas chromatography. Macromolecules 25 (1992) 949-953
158. Inoue Y., Kamiya N., Yamamoto Y., and Chûjô R. Microstructures of commerically available poly(3-hydroxybutyrate-co-3-hydroxyvalerate). Macromolecules 22 (1989) 3800-3802
159. Kamiya N., Yamamoto Y., Inoue Y., Chûjô R., and Doi Y. Microstructure of bacterially synthesized poly(3-hydroxybutyrate-co-3-hydroxy valerate). Macromolecules 22 (1989) 1676-1682
160. Bloembergen S., Holden D.A., Bluhm T.L., Hamer G.K., and Marchessault R.H. Isodimorphism in synthetic poly(β-hydroxybutyrate-co-β-hydroxyvalerate): stereoregular copolyesters from racemic β-lactones. Macromolecules 22 (1989) 1663-1669
161. Scandola M., Ceccorulli G., Pizzoli M., and Gazzano M. Study of the crystal phase and crystallization rate of bacterial poly(3-hydroxybutyrate-co-3-hydroxyvalerate). Macromolecules 25 (1992) 1405-1410
162. Wang Y., Yamada S., Asakawa N., Yamane T., Yoshie N., and Inoue Y. Comonomer compositional distribution and thermal and morphological characteristics of bacterial poly(3-hydroxybutyrate-co-3-hydroxyvalerate)s with high 3-hydroxyvalerate content. Biomacromolecules 2 (2001) 1315-1323
163. 1H NMR spectroscopy. Macromolecules 23 (1990) 1313-1317
164. 13C NMR spectroscopy and differential scanning calorimetry. Macromolecules 24 (1991) 2178-2182
165. 13C NMR determination of the degree of cocrystallization in random copolymers of poly(β-hydroxybutyrate-co-β-hydroxyvalerate). Macromolecules 28 (1995) 6394-6400
166. Kunioka M., Tamaki A., and Doi Y. Crystalline and thermal properties of bacterial copolyesters: poly(3-hydroxybutyrate-co-3-hydroxyvalerate) and poly(3-hydroxybutyrate-co-4-hydroxybutyrate). Macromolecules 22 (1989) 694-697
167. Nakamura K., Kamiya N., Sakurai M., Inoue Y., and Chûjô R. A molecular mechanics study on conformations of bacterial polyester poly(3-hydroxybutyrate-co-3-hydroxyvalerate). Polymer 33 (1992) 817-822
168. Barker P.A., Mason F., and Barham P.J. Density and crystallinity of poly(3-hydroxybutyrate/3-hydroxyvalerate) copolymers. J Mater Sci 25 (1990) 1952-1956
169. Cuesta M.S., Martínez-Salazar J., Barker P.A., and Barham P.J. Co-crystallization of poly(3-hydroxybutyrate-co-3-hydroxyvalerate). J Mater Sci 27 (1992) 5335-5338
170. Kamiya N., Sakurai M., Inoue Y., and Chûjô R. Isomorphic behavior of random copolymers: thermodynamic analysis of cocrystallization of poly(3-hydroxybutyrate-co-3-hydroxyvalerate). Macromolecules 24 (1991) 3888-3892
171. Wendling J., and Suter U.W. On the isomorphism of poly(β-hydroxybutyrate-co-β-hydroxyvalerate) random copolymers. Macromol Theory Simul 8 (1999) 110-118
172. Yoshie N., Sakurai M., Inoue Y., and Chûjô R. Cocrystallization of isothermally crystallized poly(3-hydroxybutyrate-co-3-hydroxyvalerate). Macromolecules 25 (1992) 2046-2048
173. Barham P.J., Barker P.A., and Organ S.J. Physical properties of poly(hydroxylbutyrate) and copolymers of hydroxylbutyrate and hydroxyvalerate. FEMS Microbial Rev 103 (1992) 289-298
174. Barker P.A., Barham P.J., and Martínez-Salazar J. Effect of crystallization temperature on the cocrystallization of hydroxybutyrate/hydroxyvalerate copolymers. Polymer 38 (1997) 913-919
175. Mitomo H., Morishita N., and Doi Y. Composition range of crystal phase transition of isodimorphism in poly(3-hydroxybutyrate-co-3-hydroxyvalerate). Macromolecules 26 (1993) 5809-5811
176. Mitomo H., Morishita N., and Doi Y. Structural changes of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) fractionated with acetone-water solution. Polymer 13 (1995) 2573-2578
177. Yoshie N., Menju H., Sato H., and Inoue Y. Complex composition distribution of poly(3-hydroxybutyrate-co-3-hydroxyvalerate). Macromolecules 28 (1995) 6516-6521
178. Yamada S., Wang Y., Asakawa N., Yoshie N., and Inoue Y. Crystalline structural change of bacterial poly(3-hydroxybutyrate-co-3-hydroxyvalerate) with narrow compositional distribution. Macromolecules 34 (2001) 4659-4661
179. Yoshie N., Saito M., and Inoue Y. Structural transition of lamella crystals in a isomorphous copolymer, poly(3-hydroxybutyrate-co-3-hydroxyvalerate). Macromolecules 34 (2001) 8953-8960
180. Pearce R.P., and Marchessault R.H. Melting and crystallization in bacterial poly(β-hydroxyvalerate), PHV, and blends with poly(β-hydroxybutyrate-co-hydroxyvalerate). Macromolecules 27 (1994) 3869-3874
181. Yoshie N., Menju H., Sato H., and Inoue Y. Crystallization and melting behavior in blends of poly(3-hydroxybutyrate-co-3-hydroxyvalerate)s with a narrow composition distribution. Polym J 28 (1996) 45-50
182. Saito M., Inoue Y., and Yoshie N. Cocrystallization and phase segregation of blends of poly(3-hydroxybutyrate) and poly(3-hydroxybutyrate-co-3-hydroxyvalerate). Polymer 42 (2001) 5573-5580
183. Yoshie N., Fujiwara M., Ohmori M., and Inoue Y. Temperature dependence of cocrystallization and phase segregation in blends of poly(3-hydroxybutyrate) and poly(3-hydroxybutyrate-co-3-hydroxyvalerate). Polymer 42 (2001) 8557-8563
184. Yoshie N., Saito M., and Inoue Y. Effect of chemical compositional distribution on solid-state structures and properties of poly(3-hydroxybutyrate-co-3-hydroxyvalerate). Polymer 45 (2004) 1903-1911
185. Yoshie N., Asaka A., and Inoue Y. Cocrystallization and phase segregation in crystalline/crystalline polymer blends of bacterial copolyesters. Macromolecules 37 (2004) 3770-3779
186. Yoshie N., Asaka A., Yazawa K., Kuroda Y., and Inoue Y. In situ FTIR microscope study on crystallization of crystalline/crystalline polymer blends of bacterial copolyesters. Polymer 44 (2003) 7405-7412
187. Hirota Y., Yoshie N., Ishii N., Kasuya K., and Inoue Y. Correlation between solid-state structures and enzymatic degradability of cocrystallized blends. Macromol Biosci 5 (2005) 1094-1100
188. Ouyang S.P., Luo R.C., Chen S.S., Liu Q., Chung A., Wu Q., et al. Production of polyhydroxyalkanoates with high 3-hydroxydodecanoate monomer content by fadB and fadA knockout mutant of Pseudomonas putida KT2442. Biomacromolecules 8 (2007) 2504-2511
189. Liu W., and Chen G.Q. Production and characterization of medium-chain-length polyhydroxyalkanoate with high 3-hydroxytetradecanoate monomer content by fadB and fadA knockout mutant of Pseudomonas putida KT2442. Appl Microbiol Biotechnol 76 (2007) 1153-1159
190. Cao A., Kasuya K., Abe H., Doi Y., and Inoue Y. Studies on comonomer compositional distribution of the bacterial poly(3-hydroxybutyric acid-co-3-hydroxypropionic acid)s and crystal and thermal characteristics of their fractionated component copolyesters. Polymer 39 (1998) 4801-4816
191. 13C NMR study on phase structure of the compositionally fractionated bacterial copolyester poly(3-hydroxybutyric acid-co-3-hydroxypropionic acid)s. Polymer 40 (1999) 3309-3322
192. Doi Y., Kitamura S., and Abe H. Microbial synthesis and characterization of poly(3-hydroxybutyrate-co-3-hydroxyhexanoate). Macromolecules 28 (1995) 4822-4828
193. Feng L., Watanabe T., Wang Y., Kichise T., Fukuchi T., Chen G.Q., et al. Studies on comonomer compositional distribution of bacterial poly(3-hydroxybutyrate-co-3-hydroxyhexanoate)s and thermal characteristics of their factions. Biomacromolecules 3 (2002) 1071-1077
194. Howard G.J., and Knutton S. Isomorphism in aliphatic copolyesters. Polymer 9 (1968) 527-534
195. Fuller C.S. Mixed crystal formation in linear copolyesters. J Am Chem Soc 70 (1948) 421-423
196. Papageorgiou G.Z., and Bikiaris D.N. Synthesis, cocrystallization, and enzymatic degradation of novel poly(butylene-co-propylene succinate) copolymers. Biomacromolecules 8 (2007) 2437-2449
197. Li X., Sun J., Huang Y., Geng Y., Wang X., Ma Z., et al. Inducing new crystal structures through random copolymerization of biodegradable aliphatic polyester. Macromolecules 41 (2008) 3162-3168
198. Armelin E., Casas M.T., and Puiggalí J. Structure of poly(hexamethylene sebacate). Polymer 42 (2001) 5695-5699
199. Gestí S., Almontassir A., Casas M.T., and Puiggalí J. Crystalline structure of poly(hexamethylene adipate). Study on the morphology and the enzymatic degradation of single crystals. Biomacromolecules 7 (2006) 799-808
200. Gan Z., Kuwabara K., Yamamoto M., Abe H., and Doi Y. Solid-state structures and thermal properties of aliphatic-aromatic poly(butylene adipate-co-butylene terephthalate) copolyesters. Polym Degrad Stab 83 (2004) 289-300
201. Cranston E., Kawada J., Raymond S., Morin F.G., and Marchessault R.H. Cocrystallization model for synthetic biodegradable poly(butylene adipate-co-butylene terephthalate). Biomacromolecules 4 (2003) 995-999
202. Shi X.Q., Ito H., and Kikutani T. Characterization on mixed-crystal structure and properties of poly(butylene adipate-co-terephthalate) biodegradable fibers. Polymer 46 (2005) 11442-11450
203. Shi X.Q., Aimi K., Ito H., Ando S., and Kikutani T. Characterization on mixed-crystal structure of poly(butylene terephthalate/succinate/adipate) biodegradable copolymer fibers. Polymer 46 (2005) 751-760
204. Papageorgiou G.Z., Vassiliou A.A., Karavelidis V.D., Koumbis A., and Bikiaris D.N. Novel poly(propylene terephthalate-co-succinate) random copolymers: synthesis, solid structure, and enzymatic degradation study. Macromolecules 41 (2008) 1675-1684
205. Shalaby S.W., and Kafrawy A. Synthesis and some properties of isomorphic copolymers of ε-caprolactone and 1,5-dioxepan-2-one. J Polym Sci Polym Chem Ed 27 (1989) 4423-4426
206. Dwan'Isa J.P.L., Lecomte P., Dubois P., and Jérôme R. Synthesis and characterization of random copolyesters of ε-caprolactone and 2-oxepane-1,5-dione. Macromolecules 36 (2003) 2609-2615
207. Ceccorulli G., Scandola M., Kumar A., Kalra B., and Gross R.A. Cocrystallization of random copolymers of ω-pentadecalactone and ε-caprolactone synthesized by lipase catalysis. Biomacromolecules 6 (2005) 902-907
208. Focarete M.L., Gazzano M., Scandola M., Kumar A., and Gross R.A. Copolymers of ω-pentadecalactone and trimethylene carbonate from lipase catalysis: influence of microstructure on solid-state properties. Macromolecules 35 (2002) 8066-8071
209. Kalra B., Kumar A., Gross R.A., Baiardo M., and Scandola M. Chemoenzymatic synthesis of new brush copolymers comprising poly(ω-pentadecalactone) with unusual thermal and crystalline properties. Macromolecules 37 (2004) 1243-1250
210. Papadimitriou S.A., Papageorgiou G.Z., and Bikiaris D.N. Crystallization and enzymatic degradation of novel poly(ε-caprolactone-co-propylene succinate) copolymers. Eur Polym J 44 (2008) 2356-2366
211. Schmack G., Jehnichen D., Vogel R., and Tändler B. Biodegradable fibers of poly(3-hydroxybutyrate) produced by high-speed melt spinning and spin drawing. J Polym Sci Part B: Polym Phys 38 (2000) 2841-2850
212. Iwata T., Aoyagi Y., Fujita M., Yamane H., Doi Y., Suzuki Y., et al. Processing of a strong biodegradable poly[(R)-3-hydroxybutyrate] fiber and a new fiber structure revealed by micro-beam X-ray diffraction with synchrotron radiation. Macromol Rapid Commun 25 (2004) 1100-1104
213. Iwata T., Aoyagi Y., Tanaka T., Fujita M., Takeuchi A., Suzuki Y., et al. Microbeam X-ray diffraction and enzymatic degradation of poly[(R)-3-hydroxybutyrate] fibers with two kinds of molecular conformations. Macromolecules 39 (2006) 5789-5795
214. Iwata T., and Doi Y. Mechanical properties of uniaxially cold-drawn films of poly[(R)-3-hydroxybutyrate] and its copolymers. Macromol Symp 224 (2005) 11-19
215. Tanaka F., Doi Y., and Iwata T. The deformation of the chain molecules and crystallites in poly([R]-3-hydroxybutyrate) and poly(4-hydroxybutyrate) under tensile stress. Polym Degrad Stab 85 (2004) 893-901
216. g. Polym Degrad Stab 92 (2007) 1016-1024
217. Gan Z., Kuwabara K., Abe H., Iwata T., and Doi Y. The role of polymorphic crystal structure and morphology in enzymatic degradation of melt-crystallized poly(butylene adipate) films. Polym Degrad Stab 87 (2005) 191-199
218. Zhao L., Wang X., Li L., and Gan Z. Structural analysis of poly(butylene adipate) banded spherulites from their biodegradation behavior. Polymer 48 (2007) 6152-6161
219. Feng L., Wang Y., Inagawa Y., Kasuya K., Saito T., Doi Y., et al. Enzymatic degradation behavior of comonomer compositionally fractionated bacterial poly(3-hydroxybutyrate-co-3-hydroxyvalerate)s by poly(3-hydroxyalkanoate) depolymerases isolated from Ralstonia pickettii T1 and Acidovorax sp. TP4. Polym Degrad Stab 84 (2004) 95-104